607-55-6Relevant articles and documents
Synthesis, characterization, antioxidant evaluation, molecular docking and density functional theory studies of phenyl and naphthyl based esters
Akhter, Zareen,Asghar, Muhammad Adeel,Ismail, Hammad,Kalsoom, Saima,Liaqat, Faroha,Mckee, Vickie,Sabir, Shaista,Sani, Asma,Shabbir, Muhammad,Zaib-un-Nisa
, (2020)
Two phenol based esters phenyl benzoate (OE1) and 1-naphthyl benzoate (OE2) were synthesized from phenol/1-naphthol and benzoyl chloride respectively. The structural elucidation of the synthesized compounds was accomplished by spectroscopic studies (FTIR, 1H NMR & GC-MS) and single crystal X-ray diffraction analysis. DPPH (2, 2-diphenyl-1-picryl-hydrazyl-hydrate) free radical and hydrogen peroxide activities were performed to evaluate the antioxidant capabilities of the synthesized esters. The compounds (OE1 & OE2) showed DPPH scavenging activity in concentration dependent manner with IC50 values 605.6 μM and 1138.7 μM correspondingly. Similarly, in hydrogen peroxide assay, OE1 and OE2 exhibited moderate activity with IC50 values 1510.2 μM and 1069.4 μM respectively. Molecular docking of the compounds was carried out to predict their antioxidant binding mechanism against target protein using the MOE suite. The structure?activity relationship analysis showed that replacing the phenyl ring by naphthyl significantly influences their activity. Geometrical studies of the compounds have been performed by both semi-empirical and DFT methods; results reveal an excellent convergence of experimental and theoretical structural parameters. A detailed bonding investigation of each compound has been performed by NBO and Bader's AIM analysis to obtain inter and intramolecular interactions.
Hydrogen-bond-assisted transition-metal-free catalytic transformation of amides to esters
Huang, Changyu,Li, Jinpeng,Wang, Jiaquan,Zheng, Qingshu,Li, Zhenhua,Tu, Tao
, p. 66 - 71 (2020/11/18)
The amide C-N cleavage has drawn a broad interest in synthetic chemistry, biological process and pharmaceutical industry. Transition-metal, luxury ligand or excess base were always vital to the transformation. Here, we developed a transition-metal-free hydrogen-bond-assisted esterification of amides with only catalytic amount of base. The proposed crucial role of hydrogen bonding for assisting esterification was supported by control experiments, density functional theory (DFT) calculations and kinetic studies. Besides broad substrate scopes and excellent functional groups tolerance, this base-catalyzed protocol complements the conventional transition-metal-catalyzed esterification of amides and provides a new pathway to catalytic cleavage of amide C-N bonds for organic synthesis and pharmaceutical industry. [Figure not available: see fulltext.]
Nickel-Catalyzed Cross-Coupling of Aryl Redoxactive Esters with Aryl Zinc Reagents
Shih, Bo-Hao,Basha, R. Sidick,Lee, Chin Fa
, p. 8862 - 8866 (2019/09/30)
A nickel-catalyzed aryl-aroyloxyl C(sp2)-O radical cross-coupling reaction conducted using a redox active ester with aryl zinc reagent was developed. This method demonstrates a new disconnection approach for formation of aryl aryl esters. In the one-pot sequential process, the readily available aryl carboxylic acids can be converted into functionalized aryl aryl esters and heteroaryl esters. This protocol is amenable to the gram-scale synthesis. The present method has a wide substrate scope and high functional group tolerance.
